Disazodyestuffs dyeing mordanted fibers



and Max ill l STATES iilh ll itlilt DISAZODYESTUFFS DYEING IHORDJEKNTED FlIBERii.

No Drawing.

To all ilk/1.0m 1 1i may concern:

lie it known that we, CARL Jaounsraormn lama, both citizens oi" the Bw'ss epublic. and residents of Basel, Switzerland, have imented. new Disazodyestuiis Dyeing i lordanted Fibers, of which the following is a full, clear, and exact specification".

We have found that when the aminoazodyestuil's, obtained by combining the (li2iZO derivatives of aromatic aminocarboxylic acids with aminocarboxylie acids also capable of being diazotized, preferably in form of their N-methylenesultonic acids, are diazotized again, eventually after the N-methylenesulfogroup has been split oil", and the resulting" diazobodies cmnbined with. an arylp i'razohine compound able to combine with a diazobody, new disazodyestutls are ohtaiued, which correspond to the formula wherein R and R are substituted arylrad icals which may be substituted and X. stands for an aryl iiyrazolone comeound able to be combined with a diazobody.

Particularly Valuable are the dyestuffs in which the last component. is an arylpyra H .zolone compound in which the aryl radical Ea'mnple J.

15.7 parts of anthranilie acid are dissolved in 100 parts of water and 4t parts of sodium hydroxid and condensed. .with a molecular quantity of a formaldehyde-bisullite solution derived from 3 parts of formaldehydc and 10.4- parts oi sodium bisuhite, by heating: for 8 hours at ll; to 50 The solution oi? the N-nicthyienesultocoinpound of'anthrai'iilic acid thus obtained is added,

Application filed August 17, 19 16.

Specification of Letters Patent. Pggiigmjgfl A 12313 2;?" 192g Serial No. 250,332.

in presence of sodium acetate, to the di azocompound. prepared in the usual, manner from 13.? parts oi. metaaminobenzoi acid. A tter stirring for several days at ice temperature. the diazocompound disappears and an. orange yellow dyestuii separates, which can. be salted out. The N-methylene sui'fogroup is hereaiitersplit oil in a known manner, for instance, by boiling the iilyestu'lf for 1; hour with 500 parts of soda lye of :2 per cent. The resulting -l-amiuo azo benzenet): 3-dicarboxylic acid is then isolated by acidifying with acetic acid and salting out and (Ol'lt'jliltlltGS which is dissolved again in 250 parts oi water and parts of sodium hydroxid. To the deep orauge-yellmv solution obtained are added 6 9 parts or sodium nitrite, its diazotation is eii'ectedby acidifying suddenly with l1}'(l1'0(lll()l'l0 no while ice is added and the rcs'sultinadiazoazocompound is combined with a solution of 21 parts of 1 (:2'-carbo cy)-phonyLil-methyl-5-pyrazolone made alkaline by sodium'carbonate.

The disazodyestuil' thus obtained is salted out and constitutes an orangeared powder dissolving in water to an oraiigered solution and in concentrated sulfuric acid to a tints of eood fastness.

Example 2. 21.7 parts of 3: 5-aminosulfobeuzoic acid v are diazotizwl in the usual manner and the resulting diazocompound is combined. in presence of sodium acetate, with the quan tity of tormaldehydebisulfite compound derived from 13.? parts of antliranilic acid,

indicated in ltiample 1. The monoazodyestall thus obtained is separated as described and decmuposcd by a short boiling with dilute soda lye and the resulting :baiuiuoazobenzeue-W-srdio-S:Wdicarboxylic acid is isolated by acidifying with acetic acidaud salting out. The li; 'lit.-ycllow product thus obtained is dissolved in 200 parts of water and Fl parts'oi' sodium hydroxid to'thc resulting solution are added (1.9 parts of sodium nitrite and the diazotatiou is cti'ected by acidifying suddenly with hydrochloric acidfwhile cooling with ice. The suspc11- sion of the diazoderiyative formed isadnet a lightyellow powder,

to a solution of 20.4 parts or l-phenyl-iipyraZolone-Zl-carboxylic acid made alkaline by sodium carbonate. The disazodyestutf formed is isolated by salting out and constitutes a brown-red powder dissolving in water to an orange solution and in concentrated sulfuric acid to a blue-red solution. It dyes wool in an acid bath orangeellow tints deepening to brown on a subsequent chromating. By printing it on cotton with chromium acetate a reddish-orange is obtained.

Example 3.

13.7 parts of metaaminobenzoic acid are diazotized and combined, 1n presence of sodium acetate, at ice temperature, withthe solution of formaldehyde-bisulfite compound derived from 13.7 parts of metaaminobenzoic acid. The separationand saponification are effected as in the foregoing examples. The. light-yellow product of reaction. that is to say, the 4-aminoazobenzene-.

2:3-dicarboxylic acidis dissolved in 200 parts of water and 8 parts of sodium hydroxid to the solution obtained are added parts of sodium nitrite and the diazot'athe formula coon I soui--'.\/ Example .4.

There is prepared in the known manner from. 13.7 parts of anthranilic acid the -methylene-sulfocompound which is added to the diazosoh'ltion derived. from 13.7 parts of pa 'aaminobenzoic acid. The monoazodyestufl formed is separated as described, saponified, isolated, dissolved in the form of its disodium salt, diazotized with 6.9 parts of sodium nitrite and combined with a'solution of 31.4 parts of 1 (2-oXy-3'-carboxy 5-sulfo) -phenyl-3-methyl 5-pyrazo lone made alkaline by sodium carbonate. The disazodyestufi separated by addition of common salt constitutes a red-brown powder dissolving in water with an orange-yellow coloration and in concentrated sulfuric acid with a blue-red coloration. It dyes wool in an acid bath reddish-yellow tints becoming some more brown on subsequent chromating. B printing it on cotton with chromium mor ants reddishorange-yellow tints are obtained. 7

1V hat we claim is:

1. As new products the-herein described disazodyestufi's dyeing mordanted fibers, corresponding to the formula (wherein R and R- stand for aryl radicals which may be'substituted and X designsaan arylpyrazolone compound able to be combined with a diazobody), constitutingin a dry state red to brown powders soluble in water with yellow to violet colorations and in concentrated sulfuric acid with blue-red colorations and dyeing wool in an acid bath orange-yellow to yellow-orange tints, turning, on subsequent chromating, to fast yellow to brown tints and giving, when printed on cotton with chromium mordants fast yellow to red-orange prints.

As a new article of manufacture, the herein described disazodyestufl corresponding to the formula which constitutes, in a dry state, a brown red powder dissolving in water to orange and in concentrated sulfuric acld to bluishred solutlons, dyes wool, in an ElClClbtltll, reddish-yellow tints'turning, on subsequent chromating, to a greenish-yellow and furnishes, when printed on cotton with chromium mordants, fast, pure-orange prints.

-In witness whereof we have hereunto signed our names thls 19th day of July, 1918, in the presence of two subscribing witnesses.

CARL JAGERSPACHER.

MAX ISLER.

liitnesses \VALTER E. BUNDY, (ammo BITTER 

